Try It: No One's Ever Died of Embarrassment

(NOW: You can read Dategirl every day on the Daily Weekly!) Dear Dategirl, It's been over a year and a half since a painful breakup, and I realize I haven't fully healed. I occasionally feel open to meeting sweet, attractive men, but then inevitably suffer a crisis of confidence or an about-face in my mood, and nothing comes of it. Other than this stigma of dating, I am a well-put-together 39-year-old woman who owns her own business and has wonderful friends. I suppose I am worried about past errors in judgment repeating themselves, and doubt that the people I'm attracted to could have good relationship potential. Silly that it seems I am asking for such schoolgirl advice at this age, but since I have had so few relationships—being in the last one for 18 years—perhaps I am in dire need of some perspective. —Single and Scared I've always found that one of the more shocking aspects of becoming an adult is that certain things—specifically, dating—actually become more difficult as we age. You'd think that after nearly 40 years on the planet, you'd have it down; but most of us don't, regardless of how old we are. Your cluelessness is especially understandable after having spent the last 18 years in a relationship. The last time you dated, there wasn't even a usable Internet. Now, speaking of perspective, the first thing you want to do is take a look around. Sure, you'll see a few "golden" couples who seem to have it all, but you'll also see average-looking couples, fatty-and-skinny couples, differently abled couples, and old couples. You'll also see embarrassing sugar daddies and their gold diggers, bitchy broads and their long-suffering sweeties, and cocky jackasses with a different lady for every occasion. None of these people is perfect, and all of them have someone to love. Why them and not you? Well, for one thing, they were brave enough to get out there and risk getting hurt. Obviously, timing, luck, and other variables also come into play, but without a set of stones, you're not going to be able to take advantage of anything else you have going for you. To be successful in love you have to have at least occasional moments of complete fearlessness. It only takes a second to smile and say "Hi" to a cute stranger, and if he doesn't say anything back, what have you really lost? That said, most daters suffer the occasional humiliation. So what? Nobody ever died of embarrassment. Dating can be difficult, but there are worse things than the occasional coffee date gone horribly awry. After being in a long-term relationship for so long, the tendency is to see every new assignation as your next potential long-term relationship. Unless you're a unicorn crossed with a mermaid, the chance of finding a great guy your first time (in nearly 20 years) out of the gate is slim; you're going to have to lick a few toads before you have your next psychedelic love experience. A better way to spin this is to actually avoid getting into anything serious for the next six months or a year. Instead, focus on sport dating. This way you won't be upset if the doofus your cousin fixed you up with turns out to be a World of Warcraft fanatic, and you'll be pleasantly surprised when your online date shows up and is actually better looking than his photo. You can stay home and fret that you might make a mistake, or accept that you probably will and get out there. Tell your friends to fix you up. Try online dating. Speed dating. Try anything—and report back. dategirl@seattleweekly.com